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1.
Bioorg Med Chem Lett ; 35: 127783, 2021 03 01.
Article in English | MEDLINE | ID: mdl-33422607

ABSTRACT

A new unique sesquiterpene lactone, bicyclolamellolactone A (1), was isolated together with two known monocyclofarnesol-type sesquiterpenes, lamellolactones A (2) and B (3), from the Indonesian marine sponge Lamellodysidea sp. (cf. L. herbacea). The planar structure of 1 was assigned based on its spectroscopic data (1D and 2D NMR, HRESIMS, UV, and IR spectra). The relative and absolute configuration of 1 was determined by comparison of its calculated and experimental electronic circular dichroism spectra in combination with NOESY correlations. Compounds 1-3 inhibited bone morphogenic protein (BMP)-induced alkaline phosphatase activity in mutant BMP receptor-carrying C2C12 cells with IC50 values of 51, 4.6, and 20 µM, respectively.


Subject(s)
Bone Morphogenetic Proteins/antagonists & inhibitors , Lactones/pharmacology , Osteoblasts/drug effects , Porifera/chemistry , Sesquiterpenes/pharmacology , Alkaline Phosphatase/antagonists & inhibitors , Alkaline Phosphatase/metabolism , Animals , Bone Morphogenetic Proteins/metabolism , Cell Differentiation/drug effects , Cell Line , Dose-Response Relationship, Drug , Indonesia , Lactones/chemistry , Lactones/isolation & purification , Mice , Molecular Structure , Osteoblasts/metabolism , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Structure-Activity Relationship
2.
Mar Drugs ; 18(12)2020 Nov 30.
Article in English | MEDLINE | ID: mdl-33265937

ABSTRACT

Fibrodysplasia ossificans progressiva (FOP) is a rare congenital disorder with heterotopic ossification (HO) in soft tissues. The abnormal activation of bone morphogenetic protein (BMP) signaling by a mutant activin receptor-like kinase-2 (ALK2) leads to the development of HO in FOP patients, and, thus, BMP signaling inhibitors are promising therapeutic applications for FOP. In the present study, we screened extracts of 188 Indonesian marine invertebrates for small molecular inhibitors of BMP-induced alkaline phosphatase (ALP) activity, a marker of osteoblastic differentiation in a C2C12 cell line stably expressing ALK2(R206H) (C2C12(R206H) cells), and identified five marine sponges with potent ALP inhibitory activities. The activity-guided purification of an EtOH extract of marine sponge Dysidea sp. (No. 256) resulted in the isolation of dysidenin (1), herbasterol (2), and stellettasterol (3) as active components. Compounds 1-3 inhibited ALP activity in C2C12(R206H) cells with IC50 values of 2.3, 4.3, and 4.2 µM, respectively, without any cytotoxicity, even at 18.4-21.4 µM. The direct effects of BMP signaling examined using the Id1WT4F-luciferase reporter assay showed that compounds 1-3 did not decrease the reporter activity, suggesting that they inhibit the downstream of the Smad transcriptional step in BMP signaling.


Subject(s)
Alkaline Phosphatase/antagonists & inhibitors , Cell Differentiation/drug effects , Dysidea/metabolism , Enzyme Inhibitors/pharmacology , Myoblasts, Skeletal/drug effects , Myositis Ossificans/drug therapy , Osteoblasts/drug effects , Osteogenesis/drug effects , Sterols/pharmacology , Thiazoles/pharmacology , Alkaline Phosphatase/metabolism , Animals , Bone Morphogenetic Protein 4/toxicity , Cell Line , Enzyme Inhibitors/isolation & purification , Indonesia , Mice , Molecular Structure , Myoblasts, Skeletal/metabolism , Myoblasts, Skeletal/pathology , Myositis Ossificans/metabolism , Myositis Ossificans/pathology , Osteoblasts/metabolism , Osteoblasts/pathology , Sterols/isolation & purification , Structure-Activity Relationship , Thiazoles/isolation & purification
3.
J Asian Nat Prod Res ; 22(8): 754-761, 2020 Aug.
Article in English | MEDLINE | ID: mdl-31311336

ABSTRACT

A benzyl-α-pyrone metabolite, streptpyrone A (1), was obtained together with three known isoflavonoids, daidzein-7-O-α-l-rhamnoside (2), genistein-7-O-α-l-rhamnoside (3), and daidzein (4), from the culture broth of an Indonesian actinomycete Streptomyces sp. TPU1401A. The structure of 1, elucidated based on its spectroscopic data, has been reported as a synthetic compound. However, this is the first report of the isolation of 1 as a metabolite of microbial origin. Strain TPU1401A exhibited the ability to transform the isoflavone aglycones 4 and genistein (5) into the 7-O-glycosides 2 and 3, respectively. Compounds 2 and 3 promoted the growth of strain TPU1401A more effectively than compounds 4 and 5. These results suggest that strain TPU1401A utilizes isoflavone glycosides to promote growth by transforming isoflavones through microbial glycosidation.


Subject(s)
Isoflavones , Streptomyces , Genistein , Indonesia , Molecular Structure , Pyrones
4.
Bioorg Med Chem Lett ; 28(10): 1911-1914, 2018 06 01.
Article in English | MEDLINE | ID: mdl-29631961

ABSTRACT

Callyspongiamides A (1) and B (2), two new sterol O-acyltransferase (SOAT) inhibitors, were isolated from the Indonesian marine sponge Callyspongia sp. together with a known congener, dysamide A (3). The structures of 1 and 2 were elucidated to be polychlorine-containing modified dipeptides based on their spectroscopic data. Compounds 1-3 inhibited both of the SOAT isozymes, SOAT1 and SOAT2, in cell-based and enzyme-based assays.


Subject(s)
Callyspongia/chemistry , Dipeptides/pharmacology , Enzyme Inhibitors/pharmacology , Sterol O-Acyltransferase/antagonists & inhibitors , Animals , Callyspongia/metabolism , Dipeptides/chemistry , Dipeptides/isolation & purification , Enzyme Assays , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Indonesia , Inhibitory Concentration 50 , Isoenzymes/antagonists & inhibitors , Isoenzymes/metabolism , Magnetic Resonance Spectroscopy , Molecular Conformation , Sterol O-Acyltransferase/metabolism
5.
J Nat Med ; 72(3): 779-783, 2018 Jun.
Article in English | MEDLINE | ID: mdl-29508256

ABSTRACT

Cladosporamide A (1), a new protein tyrosine phosphatase (PTP) 1B inhibitor, was isolated together with a known prenylated flavanone derivative (2) from the culture broth of an Indonesian marine sponge-derived Cladosporium sp. TPU1507 by solvent extraction, ODS column chromatography, and preparative HPLC (ODS). The structure of 1 was elucidated based on 1D and 2D NMR data. Compound 1 modestly inhibited PTP1B and T-cell PTP (TCPTP) activities with IC50 values of 48 and 54 µM, respectively. The inhibitory activity of 2 against PTP1B (IC50 = 11 µM) was approximately 2-fold stronger than that against TCPTP (IC50 = 27 µM).


Subject(s)
Cladosporium/chemistry , Porifera/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Animals , Indonesia , Protein Tyrosine Phosphatase, Non-Receptor Type 1/therapeutic use
6.
Phytochemistry ; 144: 106-112, 2017 Dec.
Article in English | MEDLINE | ID: mdl-28917090

ABSTRACT

During the search for new protein tyrosine phosphatase (PTP) 1B inhibitors, EtOH extracts from the aerial parts of Lantana camara L. (lantana) collected at Manado (Indonesia) and two subtropical islands in Japan (Ishigaki and Iriomote Islands, Okinawa) exhibited potent inhibitory activities against PTP1B in an enzyme assay. Four previously undescribed oleanane triterpenes were isolated together with known triterpenes and flavones from the Indonesian lantana. The EtOH extracts of lantana collected in Ishigaki and Iriomote Islands exhibited different phytochemical profiles from each other and the Indonesian lantana. Triterpenes with a 24-OH group were isolated from the Indonesian lantana only. Five known triterpene compounds were detected in the Ishigaki lantana, and two oleanane triterpenes with an ether linkage between 3ß and 25 were the main components together with five known triterpenes as minor components in the Iriomote lantana. The structures of previously undescribed compounds were assigned on the basis of their spectroscopic data. Among the compounds obtained in this study, oleanolic acid exhibited the most potent activity against PTP1B, and is used as a positive control in studies on PTP1B.


Subject(s)
Enzyme Inhibitors/pharmacology , Lantana/chemistry , Oleanolic Acid/analogs & derivatives , Plant Components, Aerial/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Humans , Indonesia , Japan , Molecular Structure , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Oleanolic Acid/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Structure-Activity Relationship
7.
Bioorg Med Chem Lett ; 27(15): 3503-3506, 2017 08 01.
Article in English | MEDLINE | ID: mdl-28601525

ABSTRACT

Three new dimeric 3-alkyl pyridinium alkaloids, named haliclocyclamines A-C (1-3), were isolated together with five known congeners, cyclostellettamines A (4), B (5), C (6), E (7), and F (8), from the Indonesian marine sponge Haliclona sp. The structures of 1-3 were assigned based on their spectroscopic data (1D and 2D NMR, HRFABMS, ESIMS/MS, UV, and IR). Compounds 1-8 exhibited antimicrobial activities against Mycobacterium smegmatis with inhibition zones of 17, 10, 13, 14, 8, 8, 12, and 12mm, respectively, at 10µg/disc. Compounds 3 and 8 also modestly inhibited the activity of vaccinia H-1-related phosphatase (VHR), a dual-specificity phosphatase, at 17-18µM.


Subject(s)
Alkaloids/pharmacology , Anti-Bacterial Agents/pharmacology , Haliclona/chemistry , Mycobacterium Infections, Nontuberculous/microbiology , Mycobacterium smegmatis/drug effects , Pyridinium Compounds/pharmacology , Alkaloids/chemistry , Alkaloids/isolation & purification , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Indonesia , Mycobacterium Infections, Nontuberculous/drug therapy , Pyridinium Compounds/chemistry , Pyridinium Compounds/isolation & purification
9.
J Nat Med ; 71(4): 776-779, 2017 Oct.
Article in English | MEDLINE | ID: mdl-28550651

ABSTRACT

A new biphenyl ether derivative, 2-hydroxy-6-(2'-hydroxy-3'-hydroxymethyl-5-methylphenoxy)-benzoic acid (1), was isolated together with the known benzophenone derivative, monodictyphenone (2), from a culture broth of Indonesian ascidian-derived Penicillium albobiverticillium TPU1432 by solvent extraction, ODS column chromatography, and preparative HPLC (ODS). The structure of 1 was elucidated based on NMR experiments. Compound 2 exhibited moderate inhibitory activities against protein tyrosine phosphatase (PTP) 1B, T cell PTP (TCPTP), and CD45 tyrosine phosphatase (CD45), whereas compound 1 modestly inhibited CD45 activity.


Subject(s)
Penicillium/chemistry , Phenyl Ethers/chemistry , Animals , Indonesia , Molecular Structure
10.
J Nat Med ; 71(3): 531-536, 2017 Jul.
Article in English | MEDLINE | ID: mdl-28364227

ABSTRACT

In the course of our studies on anti-mycobacterial substances from marine organisms, the known dimeric sphingolipid, leucettamol A (1), was isolated as an active component, together with the new bromopyrrole alkaloid, 5-bromophakelline (2), and twelve known congeners from the Indonesian marine sponge Agelas sp. The structure of 2 was elucidated based on its spectroscopic data. Compound 1 and its bis TFA salt showed inhibition zones of 12 and 7 mm against Mycobacterium smegmatis at 50 µg/disk, respectively, while the N,N'-diacetyl derivative (1a) was not active at 50 µg/disk. Therefore, free amino groups are important for anti-mycobacterial activity. This is the first study to show the anti-mycobacterial activity of a bisfunctionalized sphingolipid. Compound 13 exhibited weak PTP1B inhibitory activity (29% inhibition at 35 µM).


Subject(s)
Agelas/chemistry , Anti-Bacterial Agents/pharmacology , Mycobacterium smegmatis/drug effects , Pyrroles/isolation & purification , Sphingolipids/pharmacology , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Biological Products/chemistry , Biological Products/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Enzyme Inhibitors/pharmacology , Indonesia , Molecular Structure , Mycobacterium smegmatis/growth & development , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Pyrroles/chemistry , Pyrroles/pharmacology , Sphingolipids/chemistry , Sphingolipids/isolation & purification , Structure-Activity Relationship
11.
Bioorg Med Chem Lett ; 27(5): 1159-1161, 2017 03 01.
Article in English | MEDLINE | ID: mdl-28189419

ABSTRACT

Protein tyrosine phosphatase (PTP) 1B negatively regulates the insulin and leptin signaling pathways, and, thus, the clinical application of PTP1B inhibitors to the prevention and treatment of type 2 diabetes and obesity is expected. During our studies on PTP1B inhibitors, two furanosesterterpenes and a C21 furanoterpene were obtained as new types of PTP1B inhibitors from two Indonesian marine sponges. (7E, 12E, 20Z, 18S)-Variabilin (1) and (12E, 20Z, 18S)-8-hydroxyvariabilin (2) from Ircinia sp. and furospongin-1 (3) from Spongia sp. inhibited PTP1B activity with IC50 values of 1.5, 7.1, and 9.9µM, respectively. The inhibitory activity of compound 1 against T-cell PTP (TCPTP) was approximately 2-fold that against PTP1B, whereas the vaccinia H-1-related phosphatase (VHR) inhibitory effects of 1 were 4-fold weaker than that of its PTP1B inhibitory activity. Compounds 1-3 at 50µM did not show cytotoxicity against two human cancer cell lines, hepatoma Huh-7 and bladder carcinoma EJ-1. Compound 1 did not enhance the phosphorylation level of Akt, a key downstream effector of the cascade, in Huh-7 cells.


Subject(s)
Enzyme Inhibitors/pharmacology , Furans/pharmacology , Porifera/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Proteins/pharmacology , Animals , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Mice, Knockout , Protein Tyrosine Phosphatase, Non-Receptor Type 1/genetics
12.
J Nat Prod ; 80(2): 499-502, 2017 02 24.
Article in English | MEDLINE | ID: mdl-28181805

ABSTRACT

Lissoclibadins, polysulfur aromatic alkaloids, were isolated from the Indonesian ascidian Lissoclinum cf. badium. Lissoclibadins 1 (1), 3 (2), 4 (3), 7 (4), 8 (5), and 14 (6) inhibited the growth of four human solid cancer cell lines: HCT-15 (colon adenocarcinoma), HeLa-S3 (cervix adenocarcinoma), MCF-7 (breast adenocarcinoma), and NCI-H28 (mesothelioma). Lissoclibadin 1 (1) exerted the most potent cytotoxic effects in vitro and mainly promoted apoptosis through an intrinsic pathway with the activation of a caspase-dependent pathway in HCT-15 cells. In vivo studies demonstrated that 1 suppressed tumor growth in nude mice carrying HCT-15 cells without significant secondary adverse effects. In conclusion, the results obtained in the present study demonstrate that 1 has potential as a chemotherapeutic candidate for preclinical investigations.


Subject(s)
Alkaloids/isolation & purification , Alkaloids/pharmacology , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Caspases/metabolism , Urochordata/chemistry , Adenocarcinoma , Alkaloids/chemistry , Animals , Antineoplastic Agents/chemistry , Cell Proliferation/drug effects , Colonic Neoplasms/metabolism , Female , HeLa Cells , Humans , Indonesia , MCF-7 Cells , Mice , Mice, Nude , Molecular Structure
13.
Bioorg Med Chem Lett ; 27(4): 999-1002, 2017 02 15.
Article in English | MEDLINE | ID: mdl-28109786

ABSTRACT

During the search for protein tyrosine phosphatase 1B (PTP1B) inhibitors from marine organisms, the known tetramic acid derivative, melophlin C (1), was isolated as an active component together with the new nortriterpenoid saponin, sarasinoside S (2), and three homologues: sarasinosides A1 (3), I1 (4), and J (5), from the Indonesian marine sponge Petrosia sp. The structure of 2 was elucidated on the basis of its spectroscopic data. Compound 1 inhibited PTP1B activity with an IC50 value of 14.6µM, while compounds 2-5 were not active at 15.2-16.0µM. This is the first study to report the inhibitory effects of a tetramic acid derivative on PTP1B activity.


Subject(s)
Enzyme Inhibitors/pharmacology , Glycosides/pharmacology , Petrosia/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Pyrrolidinones/pharmacology , Triterpenes/pharmacology , Animals , Enzyme Inhibitors/chemistry , Glycosides/chemistry , Humans , Inhibitory Concentration 50 , Marine Biology , Pyrrolidinones/chemistry , Triterpenes/chemistry
14.
Bioorg Med Chem Lett ; 25(16): 3087-90, 2015 Aug 15.
Article in English | MEDLINE | ID: mdl-26115570

ABSTRACT

Two new merosesquiterpenes, verruculides A (1) and B (2), were isolated from a culture broth of the Indonesian ascidian-derived Penicillium verruculosum TPU1311, together with three known congeners, chrodrimanins A (3), B (4), and H (5). The structures of 1 and 2 were assigned on the basis of their spectroscopic data (1D and 2D NMR, HRMS, UV, CD, and IR). Compound 2 had a linear sesquiterpene moiety and was considered to be the derivative of the biosynthetic precursor for 1 and 3-5. Compounds 1, 3, and 5 inhibited the activity of protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 8.4, 8.5, and 14.9 µM, respectively. Compound 2 showed 40% inhibition at 23.1 µM, while 4 was not active at 20.7 µM.


Subject(s)
Enzyme Inhibitors/chemistry , Penicillium/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Sesquiterpenes/chemistry , Urochordata/microbiology , Animals , Enzyme Inhibitors/isolation & purification , Indonesia , Magnetic Resonance Spectroscopy , Molecular Conformation , Penicillium/metabolism , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Sesquiterpenes/isolation & purification
15.
J Nat Med ; 67(4): 730-5, 2013 Oct.
Article in English | MEDLINE | ID: mdl-23274914

ABSTRACT

The ethanol extract of an Indonesian marine sponge Lamellodysidea herbacea inhibited the activity of protein tyrosine phosphatase 1B (PTP1B), an important target enzyme for the treatment of type II diabetes. Bioassay-guided isolation yielded a known polybromodiphenyl ether (1) as a sole bioactive component. The structure of 1 was confirmed by spectroscopic data for 1 and its methyl ether derivative (2). Compound 1 markedly inhibited the PTP1B activity (IC50 = 0.85 µM) and showed a moderate cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells. On the other hand, compound 2 maintained potent inhibitory activity against PTP1B (IC50 = 1.7 µM) but did not show apparent cytotoxicity at 18 µM against these cancer cells. Four ester derivatives [acetyl (3), butyryl (4), hexanoyl (5), and benzoyl (6)] were prepared from 1 and their activities evaluated against PTP1B and two cancer cell lines to investigate the structure-activity relationships. Although compounds 3-6 exhibited potent inhibitory effects against PTP1B activity, cytotoxicity against HCT-15 and Jurkat cells was observed as a similar efficacy to that of 1. From these results, compound 2 was found to be the best inhibitor of PTP1B with no apparent cytotoxicity. Therefore, 2 may be a lead compound for making a new type of PTP1B inhibitor. Moreover, compound 2 did not inhibit the cell growth of Huh-7 cells (hepatoma). Hepatocytes are one of the locations of PTP1B, and Huh-7 cells are used to study the mechanism of action of compound 2.


Subject(s)
Enzyme Inhibitors/pharmacology , Halogenated Diphenyl Ethers/pharmacology , Porifera/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Animals , Cell Line, Tumor , Cell Proliferation/drug effects , Enzyme Inhibitors/chemistry , Halogenated Diphenyl Ethers/chemistry , Humans , Indonesia , Structure-Activity Relationship
16.
Nat Prod Res ; 27(11): 1012-5, 2013.
Article in English | MEDLINE | ID: mdl-22577938

ABSTRACT

The extract of an Indonesian marine sponge Haliclona sp. showed potent cytotoxicity against human solid cancer cell lines, MCF-7 (breast), LNCap (prostate), Caco-2 (colon) and HCT-15 (colon) cells. Study on nuclear morphological changes and flow cytometric analysis suggested that the component(s) in the extract would induce an apoptosis to these cancer cells. Bioassay-guided isolation yielded two pentacyclic alkaloids, papuamine (1) and haliclonadiamine (2), which inhibited cell proliferation of six human cancer cell lines with IC50 values of 0.93-1.50 and 1.00-4.44 µM, respectively. Compounds 1 and 2 accumulated lymphoma U937 cells at sub-G1 phase and induced a condensation of chromatin and fragmentation of nucleus.


Subject(s)
Alkaloids/isolation & purification , Antineoplastic Agents/isolation & purification , Porifera/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Humans
17.
Mar Drugs ; 10(2): 349-357, 2012 Feb.
Article in English | MEDLINE | ID: mdl-22412806

ABSTRACT

Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C²-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and its N-acetyl derivative (4). Compound 1 was an amide of tryptamine with two ß-alanine units. Although the planar structure of 2 is identical to that of the known compound (+)-leptoclinidamine B (5), compound 2 was determined to be the enantiomer of 5 based on amino acid analysis using HPLC methods. Compounds 1 to 4 were evaluated for cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells, but none of the compounds showed activity.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Aquatic Organisms/metabolism , Indole Alkaloids/isolation & purification , Indole Alkaloids/pharmacology , Tryptamines/isolation & purification , Tryptamines/pharmacology , Urochordata/metabolism , Acetylation , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/metabolism , Alkaloids/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/metabolism , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/metabolism , Cell Line, Tumor , Colonic Neoplasms/drug therapy , Drug Discovery , Escherichia coli/drug effects , Humans , Indian Ocean , Indole Alkaloids/chemistry , Indole Alkaloids/metabolism , Indonesia , Jurkat Cells , Ketoses/chemistry , Ketoses/isolation & purification , Ketoses/metabolism , Ketoses/pharmacology , Leukemia, T-Cell/drug therapy , Molecular Structure , Stereoisomerism , Tryptamines/chemistry , Tryptamines/metabolism , Tryptophan/analogs & derivatives , Tryptophan/chemistry , Tryptophan/isolation & purification , Tryptophan/metabolism , Tryptophan/pharmacology
18.
Steroids ; 74(9): 758-60, 2009 Sep.
Article in English | MEDLINE | ID: mdl-19375440

ABSTRACT

(25S)-3-Oxocholesta-1,4-dien-26-oic acid (1) and a new (25S)-18-acetoxy-3-oxocholesta-1,4-dien-26-oic acid (2) were isolated from a soft coral Minabea sp. (cf. aldersladei) collected in North Sulawesi, Indonesia, together with two known cholic-acid-type compounds, 3-oxochol-1,4-dien-24-oic acid (3) and 3-oxochol-4-en-24-oic acid (4). The structures of these compounds were determined on the basis of their spectroscopic data. The absolute stereochemistry at C-25 of 2 was determined by comparative (1)H NMR study using chiral anisotropic reagents [(S)- and (R)-phenylglycine methyl esters]. This is the first to report compound 1 as a natural product.


Subject(s)
Anthozoa/chemistry , Cholestenes/chemistry , Cholestenes/isolation & purification , Animals , Bacteria/drug effects , Cell Line , Cell Proliferation/drug effects , Cholestenes/pharmacology , Chromatography, High Pressure Liquid , Cricetinae , Cricetulus , Indonesia , Magnetic Resonance Spectroscopy , Mice
19.
J Antibiot (Tokyo) ; 61(7): 415-9, 2008 Jul.
Article in English | MEDLINE | ID: mdl-18776653

ABSTRACT

Two new hexahydroanthrones, tetrahydrobostrycin (1) and 1-deoxytetrahydrobostrycin (2), were isolated from a marine-derived fungus Aspergillus sp. strain 05F16 collected at the coral reef of Manado, Indonesia, together with bostrycin and abscisic acid. The structures of new compounds were determined on the basis of their spectral data. Compound 1 showed weak antibacterial activity against Staphylococcus aureus and Escherichia coli and 2 against S. aureus.


Subject(s)
Anthraquinones/isolation & purification , Anthraquinones/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Aspergillus/chemistry , Abscisic Acid , Anthraquinones/chemistry , Anti-Bacterial Agents/chemistry , Aspergillus/isolation & purification , Escherichia coli/drug effects , Indonesia , Microbial Sensitivity Tests , Molecular Structure , Seawater/microbiology , Staphylococcus aureus/drug effects
20.
Mar Biotechnol (NY) ; 7(1): 33-9, 2005.
Article in English | MEDLINE | ID: mdl-15747089

ABSTRACT

A region of 826 bp that is unlikely to code for a protein, ribosomal RNA, or transfer RNA was identified between the cytochrome b and NADH-ubiquinone oxidoreductase chain 2 loci in the mitochondrial DNA of the scleractinian reef coral Galaxea fascicularis. Nucleotide sequences were determined in a part (625 bp) of this intergenic region in 95 individuals collected at 9 sites in the Ryukyu Archipelago in southwestern Japan. A total of 8 haplotypes were found, and a deletion of 290 bp was found in 3 of them. Significant differences were found in frequencies of the haplotypes at 3 sampling sites. The presence or absence of the deletion was highly correlated with the hard or soft morphotype. The deletion was found in the majority of hard-type colonies, but in a small fraction of soft-type individuals.


Subject(s)
Anthozoa/genetics , DNA, Intergenic/genetics , DNA, Mitochondrial/genetics , Phenotype , Polymorphism, Genetic , Amino Acid Sequence , Animals , Anthozoa/anatomy & histology , Base Sequence , DNA Primers , Haplotypes/genetics , Japan , Molecular Sequence Data , Sequence Analysis, DNA
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